Simple primary amine catalyzed aerobic reductive ring-cleavage of isoxazole motif

doi:10.1016/S1872-2067(14)60200-X

Abstract

Abstract:

A clean and highly efficient catalytic aerobic reductive ring-cleavage of 3-methylanthra[1,2-c]isoxazole-6,11-dione to 1-amino-2-acetylanthraquinone was performed using simple organic amines as organocatalysts and water as a green reaction medium. This method provides a new clean transformation of isoxazole-containing compounds to the corresponding ortho-amino ketones. The catalytic performance of various organic amines was carefully screened, and simple organic primary amines were found to be promising practical catalysts with outstanding catalytic performance. Isopropylamine as the organocatalyst gave 97.2% conversion of 3-methylanthra[1,2-c]isoxazole-6,11-dione, with 97.2% selectivity to 1-amino-2-acetylanthraquinone, in the presence of oxygen only, using 1 equiv. of hydrazine hydrate at room temperature for 3 h. A possible mechanism is also proposed.

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Key words: Organocatalysis, Simple primary amine, Aerobic reductive ring cleavage, 1-Amino-2-acetyl anthraquinone, Green chemistry

Zhongkui Zhao, Renzhi Li, Yu Li, Guiru Wang. Simple primary amine catalyzed aerobic reductive ring-cleavage of isoxazole motif[J]. Chinese Journal of Catalysis, 2015, 36(2): 204-208.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(14)60200-X

https://www.cjcatal.com/EN/Y2015/V36/I2/204

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